CN105154071A - Fluorescent probe as well as preparation method and application thereof - Google Patents
Fluorescent probe as well as preparation method and application thereof Download PDFInfo
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- CN105154071A CN105154071A CN201510677189.2A CN201510677189A CN105154071A CN 105154071 A CN105154071 A CN 105154071A CN 201510677189 A CN201510677189 A CN 201510677189A CN 105154071 A CN105154071 A CN 105154071A
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Abstract
The invention discloses a fluorescent probe as well as a preparation method and application thereof. A structural formula of the fluorescent probe is shown in a formula I in the specification. The preparation method of the fluorescent probe comprises the following steps: mixing p-nitrobenzaldehyde, 2,5-dimethylpyrazine and a catalyst to obtain mixed liquor and heating the mixed liquor to 150-180 DEG C to react, thus obtaining PY-NO2; adding sodium polysulfide to PY-NO2 to react to obtain PY-NH2; adding PY-NH2, caffeic acid, triethylamine, HOBT and EDC.HCL to a mixed solvent of dichloromethane and DMF to obtain mixed liquor; and stirring the mixed liquor under the protection of an inert gas to obtain a crude product of a two-photon fluorescent probe, and purifying the crude product to obtain a pure product of the two-photon fluorescent probe. The fluorescent probe has good chemical stability and photo-physical stability, can sensitively respond to O2<.-> in acidic, neutral and alkaline ranges, has higher measurement sensitivity and is very short in response time.
Description
Technical field
The invention belongs to technical field of biological, be specifically related to a kind of fluorescent probe and preparation method thereof and application.
Background technology
The organism life-span by the impact of multiple complicated factor, such as cell mechanism and environment.A large amount of evidence show cellular energy metabolism and ROS closely related.But, up to the present, in the effect of ROS, also there is no consistent viewpoint.Much research finds that ROS participates in therefore accelerated deterioration process in cell injury.But, also have many people find the effect of the ROS signal transduction disease that can delay that ageing-related or aging itself.These dispute existence cause for the difficulty that ROS in precise monitoring living things system changes by lacking desirable instrument.Consider O
2 ˙-be first produce ROS and also other ROS can be changed into, sensitive, instantaneous spike O in live body
2˙
-for putting O in order
2 ˙-with the relation important role in life-span.The detection method of fluorescence imaging provides high spatial and temporal resolution, simultaneously little to cell injury, so be more and more considered to a kind of powerful detecting bioactive small molecule.But have better optical property for O in visual live body
2 ˙-fluorescent probe still lack very much.
Two-photon fluorescence microscope (TPFM) has a wide range of applications in living imaging field, comprising bio-sensing, oncology, neuroscience and fetology, because TPFM applies the lower photon excitation of two energy thus adds the penetration depth of tissue and decrease light injury.Therefore, a large amount of TP fluorescent probes is successfully applied to the bioactive small molecule detected in viable cell and live body.In order to study O in complex environment
2 ˙-level, can dynamic imaging O in the urgent need to construction on the impact in organism life-span
2 ˙-the TP fluorescent probe of change, this probe also needs to have good selectivity simultaneously, high TP absorption cross section and dark penetration depth.But, meet the demands at present for O in visual living tissue and complete organism
2 ˙-tP fluorescent probe still lack very much.Therefore in order to solve the problem, new imaging O
2 ˙-the optical property of fluorescent probe needs greatly to improve.
Summary of the invention
For above-mentioned prior art, the object of this invention is to provide a kind of fluorescent probe and preparation method thereof and application, this fluorescent probe has the advantage of the good and good light stability of sensitivity, selectivity.
For achieving the above object, technical scheme of the present invention is:
A kind of fluorescent probe, its structural formula is as shown in the formula shown in I:
The preparation method of above-mentioned fluorescent probe, comprises the steps:
1) preparation of PY-NO2 (2,5-bis-(4 '-nitrostyrolene base) pyrazine):
By paranitrobenzaldehyde, 2,5-dimethylpyrazine and catalyst mix obtain mixed solution, and mixed solution is heated to 150-180 DEG C, and reaction, obtains PY-NO2;
2) preparation of 2,5-bis-(4 '-aminostyryl) pyrazine (PY-NH2):
In step 1) add sodium polysulphide in the PY-NO2 that obtains, reaction, obtains PY-NH2;
3) preparation of fluorescent probe:
PY-NH2, coffic acid, triethylamine, I-hydroxybenzotriazole (HOBT) and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDC.HCL) is joined in the mixed solvent of methylene dichloride and DMF and obtain mixed solution; Described mixed solution, under the protection of rare gas element, stirs, obtains the thick product of fluorescent probe, after purifying, obtain fluorescent probe sterling.
Preferably, step 1) in, the ratio of the amount of substance of described 2,5-dimethylpyrazines, paranitrobenzaldehyde and catalyzer three is 1:(1-2.5): (1-2.5).
Further preferred, the ratio of the amount of substance of described 2,5-dimethylpyrazines, paranitrobenzaldehyde and catalyzer three is 1:2:2.
Preferably, step 1) in, described catalyzer is Tetra hydro Phthalic anhydride, benzoyl oxide or diacetyl oxide.These catalyzer not only can improve the speed of reaction of 2,5-dimethylpyrazine and paranitrobenzaldehyde effectively, effectively can also improve the transformation efficiency of raw material.
Preferably, step 1) in, described mixed solution reacts under the condition of reflux, and the time of backflow is 10-15h.
Preferably, step 1) in, the purification process of described PY-NO2, comprise the steps: step 1) in the thick product chloroform of PY-NO2 that is obtained by reacting or methylene dichloride dissolve, after washing away the catalyzer in the thick product of PY-NO2, after organic layer is separated by silica gel column chromatography, obtain PY-NO2 sterling.
Preferred further, the solution washing away catalyzer in the thick product of PY-NO2 is saturated sodium hydroxide solution, saturated sodium carbonate solution or saturated potassium hydroxide solution.These saturated solutions can remove the catalyzer in the thick product of PY-NO2 up hill and dale, make the PY-NO2 obtained purer.
Preferably, step 2) in, PY-NO2 is 1:1-1:10 with the ratio of the amount of substance of sodium polysulphide.
Preferably, step 2) in, the mixture of PY-NO2 and sodium polysulphide refluxes 3-5h in the ethanolic soln of 95%, and reflux temperature is 78 DEG C, obtained PY-NH2.The boiling point of the ethanolic soln of 95% is 78 DEG C, and can ensure in the process of reacting by heating, the temperature of reactant maintains 78 DEG C, both ensure that speed of reaction, additionally reduces the by product that reaction produces.
Preferably, step 3) in, described PY-NH2, coffic acid, triethylamine, the amount of substance of HOBT and EDC.HCL is than being 1:(2-3.5): (2-3.5): (2-3.5): (2-3.5).Wherein, HOBT, EDC.HCL are catalysts, and effect is the caffeinic carboxyl of activation.
Preferably, step 3) in, the ratio of PY-NH2 and mixed solvent is 1mmol:(8-30) ml.
Preferably, step 3) in, in described mixed solvent, DMF and CH
2cl
2volume ratio be 1:2-6.The mixed solvent of this component proportion can abundant solubilizing reaction thing, and reaction is carried out smoothly.
Preferably, step 3) in, the purification process of the thick product of fluorescent probe, the thick product obtained is comprised the steps: to concentrate, thick product after concentrated is carried out TLC separation, eluent is methyl alcohol, toluene and ethyl acetate mixtures, and wherein, the volume ratio of methyl alcohol, toluene and ethyl acetate is 1:6-10:2-6.Fluorescent probe can elute by this eluent effectively, and other Impurity elution can not be got off, and this eluent is easy and product separation, ensure that the purity of the product after wash-out.
Preferred further, in described eluent, the volume ratio of methyl alcohol, toluene and ethyl acetate is 1:8:4.
Fluorescent probe of the present invention, one-photon excitation wavelength is 400nm, and two-photon excitation wavelength is 800nm, and maximum emission wavelength is 520nm.
The application of above-mentioned fluorescent probe in detection cell or in intravital superoxide anion.
The method of above-mentioned fluorescent probe detection cell or in vivo superoxide anion is: with the solution incubated cell containing fluorescent probe or live body, after hatching setting-up time, wash away unnecessary fluorescent probe molecule, then carry out Laser scanning confocal microscopy.
Preferably, described solution is comprise damping fluid or the water-miscible organic solvent that pH value is 7.4 in physiological saline, buffering range.
Preferably, the concentration of described buffered soln is 0.01-0.05mol/L.
Preferably, the described concentration containing the fluorescent probe in the solution of fluorescent probe is 1-10 μm of ol/L.The fluorescent probe of this concentration can carry out imaging preferably to cell or live body.
Beneficial effect of the present invention is:
(1) chemical stability of fluorescent probe of the present invention, optical physics good stability; Fluorescent probe of the present invention within the scope of the pH of acid, neutral and alkaline wide such as grade to O
2 ˙-sensitivity can be responded, with O
2 ˙-reacted fluorescence intensity at least can strengthen 5 times, measure sensitivity higher, and the time of response is extremely short.
(2) fluorescent probe of the present invention is to O
2 ˙-there is good selectivity, hydrogen peroxide (H
2o
2), tertbutyl peroxide (TBHP), hypochlorite (OCl
-), singlet oxygen (
1o
2), peroxidation nitrosyl (ONOO
-), hydroxyl radical free radical (OH), nitrogen protoxide (NO), and metal cations Fe
3+, Fe
2+, Cu
2+, Cu
+with Zn
2+to detection not interference; Probe molecule cell permeability is good, does not have toxic side effect to cell, is suitable for O in cell
2 ˙-the detection of change in concentration.
(3) fluorescent probe of the present invention is to O
2 ˙-response be reversible reaction, reversible reaction can realize dynamic, real-time observation O
2 ˙-change.
(4) synthesis step of fluorescent probe of the present invention is simple, easy purifying.
Accompanying drawing explanation
Fig. 1 is two-photon fluorescence intensity and the O of probe I of the present invention
2 ˙-the relation of change, wherein, X-coordinate is wavelength (nm), and ordinate zou is fluorescence intensity;
Fig. 2 is the fluorescence intensity of probe I of the present invention and the O of different concns
2 ˙-titration curve, wherein, X-coordinate is wavelength (nm), and ordinate zou is fluorescence intensity, and the little figure X-coordinate of upper right is O
2 ˙-concentration, ordinate zou is fluorescence intensity;
Fig. 3 is the selectivity schematic diagram of probe I of the present invention.10 μMs of probes I of the present invention are to the fluorescence response (20mMH in different active oxygens and active nitrogen 60min
2o
2, 200 μMs of TBHP, 200 μMs of NaClO, 200 μMs
1o
2, 33 μMs of ONOO
–, 200 μMs
.oH, 200 μMs of NO and O
2 ˙-20 μMs), icon is the different test duration (0 to 60min).
Fig. 4 is O in probe of the present invention I pair of HepG2 cell
2 ˙-two-photon in situ imaging.Wherein, in figure, b, d are liver cancer cell imaging after 2-methyl estradiol stimulates; C, e are for adding O
2 ˙-fluorescence imaging after xitix.
Embodiment
The present invention is further illustrated in conjunction with specific embodiments, should be noted that following explanation is only to explain the present invention, not limiting its content.
The synthesis of embodiment 1:PY-NH2
Step is as follows:
2,5-bis-(4 '-aminostyryl) pyrazine (PY-NH2): add paranitrobenzaldehyde (7.55g in 250mL there-necked flask, 0.05mol), 2,5-dimethylpyrazine (3.24g, 0.01mol) with Tetra hydro Phthalic anhydride (7.40g, 0.05mol).Be heated to 180 DEG C, after backflow 15h, be cooled to room temperature, dissolve with 50mL chloroform.Solution is with after 5% sodium hydroxide solution extraction, and organic layer is separated (leacheate is n-hexane/ethyl acetate=2/1) by silica gel column chromatography, obtains PY-NO2.In PY-NO2, add 10ml sodium polysulphide, reflux 3h in ethanolic soln, obtains PY-NH2.
PY-NH2.
1HNMR(400MHz,DMSO):δ8.55(s,4H),δ8.43(s,2H),δ7.56(d,J＝16.0,2H),δ7.35(d,J＝8.0,4H),δ6.99(d,J＝16.0,2H),δ6.59(d,J＝8.0,4H)；
13CHNMR(400MHz,DMSO):δ150.27,144.11,142.27,134.29,129.08,129.01,118.95,114.31；MSdata,m/zcalcdfor[C
20H
18N
4+H]315.1565,found315.1600.
Embodiment 2: the synthesis of fluorescent probe
The synthesis step of PY-CA is as follows: add PY-NH2 (0.314g in 250mL there-necked flask, 1.0mmol), coffic acid (0.525g, 3.0mmol), triethylamine (1.0mL), HOBT (0.636g, 3.0mmol) and EDC (0.576g, 3.0mmol) is in the mixed solvent of methylene dichloride (8.0mL) and DMF (1.2mL).Under the protection of argon gas, mixed solution, in stirred overnight at room temperature, obtains thick product.After falling partial solvent by rotary evaporation, product carries out TLC separation (silica gel G F
254), eluent is toluene and methanol/ethyl acetate=4/0.5/2, obtains yellow product.
Embodiment 3: the synthesis of fluorescent probe
The synthesis step of PY-CA is as follows: add PY-NH2 (1.0mmol) in 250mL there-necked flask, coffic acid (2.0mmol), triethylamine (1.0mL), HOBT (2.0mmol) and EDC (3.5mmol) is in the mixed solvent of methylene dichloride (8.0mL) and DMF (3.0mL).Under the protection of argon gas, mixed solution, in stirred overnight at room temperature, obtains thick product.After falling partial solvent by rotary evaporation, product carries out TLC separation (silica gel G F
254), eluent is toluene and methanol/ethyl acetate=6/1/4, obtains yellow product.
PY-CA.
1HNMR(400MHz,DMSO):δ8.30(s,2H),δ8.16(d,J＝8.0,4H),δ7.92(d,J＝8.0,4H),δ7.9278(d,J＝16.0,2H),δ7.63(d,J＝8.0,4H),δ7.47(d,J＝16.0,2H),δ7.45(d,J＝16.0,2H),δ7.43(s,4H),δ7.37(d,J＝16.0,2H),δ7.35(s,4H)；
13CHNMR(400MHz,DMSO):δ164.38,162.96,143.24,132.48,132.03,129.58,129.13,128.26,127.94,125.96,124.34,120.20,110.08,113.40,110.72,110.19,106.87；MSdata,m/zcalcdfor[C
38H
30N
4O
6+H]639.2165,found639.2265.
Embodiment 4 effect experimental
(1) probe I couple of O
2 ˙-responsiveness experiment
The probe I using embodiment 1 to synthesize evaluates it to O
2 ˙-responsiveness
The probe I that the embodiment 1 of 10 μMs is synthesized is joined Tris buffering, pH7.4, one-photon excitation wavelength is 400nm, and two-photon excitation wavelength is 800nm, and maximum emission wavelength is 520nm.When adding O
2 ˙-after, single photon and the two-photon fluorescence of probe all obviously strengthen.Test result as shown in Figure 1 and Figure 2.Fig. 1 is fluorescence spectrum, and Fig. 2 is titration curve.From Fig. 1 and Fig. 2, probe I couple of O
2 ˙-change response is responsive, can as O
2 ˙probe uses.
(2) O in probe I pair of cell
2 ˙-fluorescence imaging
HepG2 cell (being selected from the American Type Culture Collection council of Chinese Academy of Sciences cell bank) is cultivated by the DMEM nutrient solution (Gibco) of high sugar, before imaging, cell attachment is on cover glass, and in same ware cell, circulation adds stimulant 2-methyl estradiol (1.0 μ g/mL) and reductive agent xitix 1.0mM.In Fig. 4, lower of a room temperature 10 μMs of probe incubated cells 10 minutes; B and d10 μM of probe hatch after cell, hatch 30 minutes with-methyl estradiol (1.0 μ g/mL); Cell after c, e-methyl estradiol stimulates, then hatch 30 minutes with the xitix of 1.0mM.F, before adding 10 μMs of probes, hatches 30 minutes with the cell that 2-ME stimulates with 10 μMs of ferrotianium scavenging agents.Two-photon excitation wavelength is 800nm, collects and is emitted as 500-550nm.Can see that probe can to O in cell
2 ˙-carry out visual research.
By reference to the accompanying drawings the specific embodiment of the present invention is described although above-mentioned; but the restriction not to invention protection domain; one of ordinary skill in the art should be understood that; on the basis of technical scheme of the present invention, those skilled in the art do not need to pay various amendment or distortion that creative work can make still in protection scope of the present invention.
Claims (10)
1. a fluorescent probe, is characterized in that: its structural formula is as shown in the formula shown in I:
2. the preparation method of fluorescent probe according to claim 1, is characterized in that: comprise the steps:
1) preparation of PY-NO2:
By paranitrobenzaldehyde, 2,5-dimethylpyrazine and catalyst mix obtain mixed solution, and mixed solution is heated to 150-180 DEG C, and reaction, obtains PY-NO2;
2) preparation of PY-NH2:
In step 1) add sodium polysulphide in the PY-NO2 that obtains, reaction, obtains PY-NH2;
3) preparation of fluorescent probe:
PY-NH2, coffic acid, triethylamine, HOBT and EDC.HCL are joined in the mixed solvent of methylene dichloride and DMF and obtain mixed solution; Described mixed solution, under the protection of rare gas element, stirs, obtains the thick product of fluorescent probe, after purifying, obtain fluorescent probe sterling.
3. preparation method according to claim 2, is characterized in that: step 1) in, the ratio of the amount of substance of described 2,5-dimethylpyrazines, paranitrobenzaldehyde and catalyzer three is 1:(1-2.5): (1-2.5).
4. preparation method according to claim 2, is characterized in that: step 1) in, described catalyzer Tetra hydro Phthalic anhydride, benzoyl oxide or diacetyl oxide.
5. preparation method according to claim 2, it is characterized in that: step 1) in, the purification process of described PY-NO2, comprise the steps: step 1) in the thick product chloroform of PY-NO2 that is obtained by reacting or methylene dichloride dissolve, after washing away the catalyzer in the thick product of PY-NO2, after organic layer is separated by silica gel column chromatography, obtain PY-NO2 sterling.
6. preparation method according to claim 2, is characterized in that: step 2) in, the mixture of PY-NO2 and sodium polysulphide refluxes 3-5h, obtained PY-NH2 in the ethanolic soln of 95%.
7. preparation method according to claim 2, it is characterized in that: step 3) in, the purification process of the thick product of fluorescent probe, the thick product obtained is comprised the steps: to concentrate, thick product after concentrated is carried out TLC separation, eluent is methyl alcohol, toluene and ethyl acetate mixtures, and wherein, the volume ratio of methyl alcohol, toluene and ethyl acetate is 1:6-10:2-6.
8. the application in detection cell or in intravital superoxide anion according to claim 1.
9. application according to claim 8, it is characterized in that: described in the fluorescent probe the stated method that detects cell or in vivo superoxide anion be: with the solution incubated cell containing fluorescent probe or live body, after hatching setting-up time, wash away unnecessary fluorescent probe molecule, then carry out Laser scanning confocal microscopy.
10. application according to claim 9, is characterized in that: described solution is comprise damping fluid or the water-miscible organic solvent that pH value is 7.4 in physiological saline, buffering range.
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| CN106565628A (en) * | 2016-11-15 | 2017-04-19 | 济南大学 | Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof |
| CN107884349A (en) * | 2017-10-13 | 2018-04-06 | 昆明理工大学 | The assay method of ultra-oxygen anion free radical in a kind of microbial body |
| CN108129376A (en) * | 2017-11-28 | 2018-06-08 | 中国科学院烟台海岸带研究所 | Organic compound, intermediate and application based on flower cyanines |
| CN111100184A (en) * | 2019-12-19 | 2020-05-05 | 山东师范大学 | Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof |
| CN112313203A (en) * | 2018-06-22 | 2021-02-02 | 松下电器产业株式会社 | Organic salt, and hydroxyl radical sensor and detection medium provided with same |
| CN112881355A (en) * | 2021-01-17 | 2021-06-01 | 复旦大学 | Double-parameter fluorescent nano sensor for simultaneously measuring pH and oxygen concentration in cells and preparation method thereof |
| CN114437053A (en) * | 2021-12-22 | 2022-05-06 | 山东师范大学 | Nano probe and application thereof in detecting superoxide anion in Golgi apparatus |
| CN114456079A (en) * | 2021-12-23 | 2022-05-10 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
| CN114736163A (en) * | 2022-05-12 | 2022-07-12 | 深圳先进电子材料国际创新研究院 | Nitrogen-containing heterocyclic diamine compound, preparation method thereof, polyimide precursor, polyimide film and application thereof |
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Cited By (16)
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| CN106565628A (en) * | 2016-11-15 | 2017-04-19 | 济南大学 | Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof |
| CN107884349A (en) * | 2017-10-13 | 2018-04-06 | 昆明理工大学 | The assay method of ultra-oxygen anion free radical in a kind of microbial body |
| CN107884349B (en) * | 2017-10-13 | 2020-12-15 | 昆明理工大学 | Determination method of superoxide anion free radicals in microorganisms |
| CN108129376A (en) * | 2017-11-28 | 2018-06-08 | 中国科学院烟台海岸带研究所 | Organic compound, intermediate and application based on flower cyanines |
| CN112313203B (en) * | 2018-06-22 | 2023-05-02 | 松下控股株式会社 | Organic salt, hydroxyl radical sensor comprising same, and detection medium |
| CN112313203A (en) * | 2018-06-22 | 2021-02-02 | 松下电器产业株式会社 | Organic salt, and hydroxyl radical sensor and detection medium provided with same |
| CN111100184A (en) * | 2019-12-19 | 2020-05-05 | 山东师范大学 | Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof |
| CN111100184B (en) * | 2019-12-19 | 2021-08-17 | 山东师范大学 | Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof |
| CN112881355A (en) * | 2021-01-17 | 2021-06-01 | 复旦大学 | Double-parameter fluorescent nano sensor for simultaneously measuring pH and oxygen concentration in cells and preparation method thereof |
| CN114437053A (en) * | 2021-12-22 | 2022-05-06 | 山东师范大学 | Nano probe and application thereof in detecting superoxide anion in Golgi apparatus |
| CN114437053B (en) * | 2021-12-22 | 2023-12-01 | 山东师范大学 | Nanometer probe and application thereof in detecting superoxide anions in golgi |
| CN114456079A (en) * | 2021-12-23 | 2022-05-10 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
| CN114456079B (en) * | 2021-12-23 | 2023-06-23 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
| CN114736163A (en) * | 2022-05-12 | 2022-07-12 | 深圳先进电子材料国际创新研究院 | Nitrogen-containing heterocyclic diamine compound, preparation method thereof, polyimide precursor, polyimide film and application thereof |
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